Betamethasone acetate | CAS#987-24-6

MedKoo Cat#: 330172 | Name: Betamethasone acetate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Betamethasone acetate, also known as Betamethasone 21-acetate, is a synthetic glucocorticoid corticosteroid and a corticosteroid ester. It is the 21-acetate ester of betamethasone.

Chemical Structure

Betamethasone acetate

CAS#987-24-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 330172

Name: Betamethasone acetate

CAS#: 987-24-6 (acetate)

Chemical Formula: C24H31FO6

Exact Mass: 434.2105

Molecular Weight: 434.50

Elemental Analysis: C, 66.34; H, 7.19; F, 4.37; O, 22.09

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 weeks
2g	USD 550.00	2 Weeks
5g	USD 1,050.00	2 weeks

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Related CAS #

378-44-9 (free acid) 5534-05-4 (acibutate) 987-24-6 (acetate) 5593-20-4 (dipropionate) 151-73-5 (sodium phosphate) 2152-44-5 (valerate) 22298-29-9 (benzoate)

Synonym

Betamethasone acetate; Betamethasone 21-acetate;

IUPAC/Chemical Name

9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 21-acetate

InChi Key

AKUJBENLRBOFTD-QZIXMDIESA-N

InChi Code

InChI=1S/C24H31FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,13,17-19,28,30H,5-6,9,11-12H2,1-4H3/t13-,17-,18-,19-,21-,22-,23-,24-/m0/s1

SMILES Code

C[C@@]12[C@](C(COC(C)=O)=O)(O)[C@@H](C)C[C@@]1([H])[C@]3([H])CCC4=CC(C=C[C@]4(C)[C@@]3(F)[C@@H](O)C2)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Betamethasone is a glucocorticoid with anti-inflammatory and immunosuppressive activities.

In vitro activity:

After treatment with anti-inflammatory drugs, betamethasone (BMS) and peripheral blood mononuclear cells (PBMCs) were exposed to HIV NL4-3 AD8. Multiplexed ELISA was used to measure 28 cytokines to assess inflammation. Flow cytometry was used to measure immune activation (CD38, HLA-DR and CCR5) and HIV infection (p24 production) of CD4+ T cells. BMS potently suppressed inflammation (soluble cytokines, p<0.05) and immune activation (CD4+ T cells, p<0.05). BMS significantly reduced HIV infection of CD4+ T cells only in the LPS (0.98%) and unstimulated (1.7%) conditions (p<0.02). BMS demonstrated potent anti-inflammatory effects, regardless of stimulation condition. Despite uniform immunosuppression, BMS differentially affected HIV infection according to the stimulation conditions, highlighting the complex nature of these interactions. Reference: J Investig Med. 2021 Jan;69(1):28-40. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7803916/

In vivo activity:

Whether betamethasone alters the immunohistochemical expression of proteins that participate in cerebellar Purkinje cell dendritic development and maintenance, including microtubule-associated protein 2 (MAP2), brain-derived neurotrophic factor (BDNF) and the tyrosine kinase B receptor (TrkB), which are located predominantly in the cerebellar molecular layer where Purkinje cell dendritogenesis occurs, was evaluated. It was observed that rats prenatally exposed to a single course of betamethasone showed long-term alterations in the expression of MAP2, BDNF and TrkB. Additionally, these protracted molecular changes were accompanied by anxiety-like behaviors in the elevated plus maze and marble burying tests. Reference: Int J Dev Neurosci. 2015 Jun;43:78-85. https://onlinelibrary.wiley.com/doi/abs/10.1016/j.ijdevneu.2015.04.005

Preparing Stock Solutions

The following data is based on the product molecular weight 434.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cromarty R, Sigal A, Liebenberg LJ, Mckinnon LR, Abdool Karim SS, Passmore JS, Archary D. Betamethasone induces potent immunosuppression and reduces HIV infection in a PBMC in vitro model. J Investig Med. 2021 Jan;69(1):28-40. doi: 10.1136/jim-2020-001424. Epub 2020 Oct 1. PMID: 33004468; PMCID: PMC7803916. 2. Pascual R, Valencia M, Bustamante C. Antenatal betamethasone produces protracted changes in anxiety-like behaviors and in the expression of microtubule-associated protein 2, brain-derived neurotrophic factor and the tyrosine kinase B receptor in the rat cerebellar cortex. Int J Dev Neurosci. 2015 Jun;43:78-85. doi: 10.1016/j.ijdevneu.2015.04.005. Epub 2015 Apr 15. PMID: 25889225.

In vitro protocol:

In vivo protocol:

1. Pascual R, Valencia M, Bustamante C. Antenatal betamethasone produces protracted changes in anxiety-like behaviors and in the expression of microtubule-associated protein 2, brain-derived neurotrophic factor and the tyrosine kinase B receptor in the rat cerebellar cortex. Int J Dev Neurosci. 2015 Jun;43:78-85. doi: 10.1016/j.ijdevneu.2015.04.005. Epub 2015 Apr 15. PMID: 25889225.

1: Ehling S, Baynes RE, Bäumer W. Impact of synthetic canine cerumen on in vitro penetration of auricular skin of dogs by florfenicol, terbinafine, and betamethasone acetate. Am J Vet Res. 2018 Mar;79(3):333-341. doi: 10.2460/ajvr.79.3.333. PubMed PMID: 29466046. 2: Schmidt AF, Kemp MW, Rittenschober-Böhm J, Kannan PS, Usuda H, Saito M, Furfaro L, Watanabe S, Stock S, Kramer BW, Newnham JP, Kallapur SG, Jobe AH. Low-dose betamethasone-acetate for fetal lung maturation in preterm sheep. Am J Obstet Gynecol. 2018 Jan;218(1):132.e1-132.e9. doi: 10.1016/j.ajog.2017.11.560. Epub 2017 Nov 11. PubMed PMID: 29138038; PubMed Central PMCID: PMC5759749. 3: Noli C, Sartori R, Cena T. Impact of a terbinafine-florfenicol-betamethasone acetate otic gel on the quality of life of dogs with acute otitis externa and their owners. Vet Dermatol. 2017 Aug;28(4):386-e90. doi: 10.1111/vde.12433. Epub 2017 Mar 15. PubMed PMID: 28295766. 4: Menendez MI, Phelps MA, Bertone AL. Pharmacokinetics of intra-articular betamethasone sodium phosphate and betamethasone acetate and endogenous hydrocortisone suppression in exercising horses. J Vet Pharmacol Ther. 2016 Feb;39(1):22-6. doi: 10.1111/jvp.12229. Epub 2015 Apr 3. PubMed PMID: 25847081. 5: Habib G, Artul S, Chernin M, Hakim G, Jabbour A. The effect of intra-articular injection of betamethasone acetate/betamethasone sodium phosphate at the knee joint on the hypothalamic-pituitary-adrenal axis: a case-controlled study. J Investig Med. 2013 Oct;61(7):1104-7. doi: 10.2310/JIM.0b013e3182a67871. PubMed PMID: 24013525. 6: Habib G, Artul S, Hakim G. Annoying Hiccups following Intra-Articular Corticosteroid Injection of Betamethasone Acetate/Betamethasone Sodium Phosphate at the Knee Joint. Case Rep Rheumatol. 2013;2013:829620. doi: 10.1155/2013/829620. Epub 2013 Mar 14. PubMed PMID: 23573452; PubMed Central PMCID: PMC3612444. 7: Salem II, Najib NM. Pharmacokinetics of betamethasone after single-dose intramuscular administration of betamethasone phosphate and betamethasone acetate to healthy subjects. Clin Ther. 2012 Jan;34(1):214-20. doi: 10.1016/j.clinthera.2011.11.022. Epub 2011 Dec 9. PubMed PMID: 22154197. 8: Rafienia M, Emami SH, Mirzadeh H, Mobedi H, Karbasi S. Influence of poly (lactide-co-glycolide) type and gamma irradiation on the betamethasone acetate release from the in situ forming systems. Curr Drug Deliv. 2009 Apr;6(2):184-91. PubMed PMID: 19450225. 9: Habib G, Safia A. The effect of intra-articular injection of betamethasone acetate/betamethasone sodium phosphate on blood glucose levels in controlled diabetic patients with symptomatic osteoarthritis of the knee. Clin Rheumatol. 2009 Jan;28(1):85-7. doi: 10.1007/s10067-008-1023-9. Epub 2008 Oct 14. PubMed PMID: 18853221. 10: Ke X, Ping Q, Liao Z. Interconversion kinetic studies of betamethasone acetate polymorphs in water. Drug Dev Ind Pharm. 2006 Oct;32(9):1019-24. PubMed PMID: 17012114. 11: Ke X, Ping Q, Shi H. Interconversion studies of betamethasone acetate polymorphs. Drug Dev Ind Pharm. 2005 Sep;31(8):813-8. PubMed PMID: 16221616. 12: Subtil D, Tiberghien P, Devos P, Therby D, Leclerc G, Vaast P, Puech F. Immediate and delayed effects of antenatal corticosteroids on fetal heart rate: a randomized trial that compares betamethasone acetate and phosphate, betamethasone phosphate, and dexamethasone. Am J Obstet Gynecol. 2003 Feb;188(2):524-31. PubMed PMID: 12592266. 13: Petersen MC, Nation RL, Ashley JJ. Simultaneous determination of betamethasone, betamethasone acetate and hydrocortisone in biological fluids using high-performance liquid chromatography. J Chromatogr. 1980 Aug 8;183(2):131-9. PubMed PMID: 7400271. 14: Macera C, de la Sota F, Gálvez S. [Treatment of lumbar sciatica with epidural injections of betamethasone acetate-phosphate (author's transl)]. Rev Med Chil. 1978 Sep;106(9):699-704. Spanish. PubMed PMID: 152964. 15: Vespasiani A, Pagliughi G. [Betamethasone acetate in the therapy of epicondylitis]. Chir Ital. 1976 Dec;28(6):958-61. Italian. PubMed PMID: 1029542. 16: Tosi S, Fantini F, Solazzi F. [Local use of an association of bisodium phosphate of betamethasone and of betamethasone acetate in rheumatological patients]. Recenti Prog Med. 1970 Mar;48(3):XXI-XXXV. Italian. PubMed PMID: 5467922. 17: Bonomo I, Vianna U, Reis SS, Vieira WP, Netto RT. [Comparative test of the intra-articular use of the combination phosphate plus betamethasone acetate and 6-methylprednisolone]. Hospital (Rio J). 1969 Nov;76(5):1685-92. Portuguese. PubMed PMID: 5308966. 18: Husby G. [Local injection therapy with a new injectable steroid preparation, betamethasone binatriumphosphate-betamethasone-acetate (Celestone-Chronodose)]. Tidsskr Nor Laegeforen. 1967 Jun 15;87(12):1160-2. Norwegian. PubMed PMID: 5599184. 19: Gómez Carpio M, Kandora H, Rojas L. [Local treatment of some rheumatologic diseases with betamethasone acetate and betamethasone disodium phosphate]. Rev Med Chil. 1965 Apr;93(4):168-71. Spanish. PubMed PMID: 5294398.

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